There is little published research that examines the supervision experience of field attachment supervisors in Kenya. In this study, we identify the challenges encountered by field supervisors during student field attachments with community organizations. Fifteen organizations that had hosted third year students from the Department of Community Resource Management and Extension (CRM&E) at Kenyatta University during their practicum attachment were sampled using purposive and convenience sampling. Data was collected using face-to-face key informant interviews with field supervisors (n = 15). Data was analyzed using NVivo10 software for qualitative analysis. Thematic analysis resulted in the identification of key themes related to clarity of learning objectives for students and the supervision challenges encountered by field supervisors during practicum. Key findings indicate that the supervisors largely lacked a clear understanding of practicum expectations and the academic preparation of students in the Community Resource Management and Extension program. The main supervision challenge is largely on orienting students to community based field work so as to enable them link theory to practice. These results can be helpful for any academic program to improve the field attachment experience of university students and the community organizations hosting the students. A better understanding of the challenges that field supervisors' encounter is fundamental to the enhancement of the practicum experience of university students since the requisite and appropriate support can be provided to the host organizations. Subsequently, the students will be more likely to optimize the intended benefits of the practicum as a result of the host organizations enhancing the quality of field-based learning.